600-40-8

Basic information

• Product Name: 1,1-DINITROETHANE
• Synonyms: 1,1-DINITROETHANE
• CAS NO: 600-40-8
• Molecular Formula: C₂H₄N₂O₄
• Molecular Weight: 120.06
• Mol File: 600-40-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 39.5°C (estimate)
• Boiling Point: 185.55°C
• Flash Point: 79°C
• Appearance: /
• Density: 1.3490
• Refractive Index: 1.4468 (estimate)
• PKA: pK1:5.21 (25°C)
• CAS DataBase Reference: 1,1-DINITROETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DINITROETHANE(600-40-8)
• EPA Substance Registry System: 1,1-DINITROETHANE(600-40-8)

Safety Data

• Hazardous Substances Data: 600-40-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 83, p. 3535, 1961 DOI: 10.1021/ja01477a047

Safety Profile

A poison by intraperitoneal route. An unstable solid forbidden for transport. When heated to decomposition it emits toxic vapors of NOx

Synthetic route

1,1-dinitrobromoethane (5432-38-2) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With sodium thiophenolate In N,N-dimethyl-formamide Irradiation;	89%
With ethanol; hydrazine

nitroform potassium salt + methyl iodide (74-88-4) → 1,1-dinitroethane (600-40-8) + 1,1,1-trinitroethane (595-86-8)

Conditions	Yield
15-crown-5 at 20℃; Yield given;	A n/a B 79%
15-crown-5 at 20℃; Yields of byproduct given;	A n/a B 79%

Nitroethane (79-24-3) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With sodium hydroxide; sodium persulfate; potassium hexacyanoferrate(III); sodium nitrite In dichloromethane at 25℃; for 1h;	60%
at 37℃; for 8h; 2-nitropropane oxidase;
With sodium hydroxide; sodium nitrite In dichloromethane; water at 8 - 10℃; Electrochemical reaction;	35 % Turnov.

1,1-dinitroethane potassium salt (2517-91-1) → 1,1-dinitroethane (600-40-8) + 1-chloro-1,1-dinitro-ethane (2972-95-4) + 1,1,1-trinitroethane (595-86-8) + acetic acid (64-19-7)

Conditions	Yield
With xenon difluoride; water; dinitrogen tetraoxide In dichloromethane for 8h; Ambient temperature; Further byproducts given;	A 56.1% B 12.1 % Chromat. C 22.0 % Chromat. D 2.3 % Chromat.
With xenon difluoride; water; dinitrogen tetraoxide In dichloromethane for 8h; Ambient temperature; Further byproducts given;	A 56.1 % Chromat. B 12.1 % Chromat. C 22% D 2.3 % Chromat.

1,1-dinitroethane potassium salt (2517-91-1) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With hydrogenchloride In dichloromethane at 20℃; for 1h;	36%

phenyl 1,1-dinitroethyl selenide (78743-51-8) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With hydrogenchloride In dichloromethane at 20℃; for 1h; Product distribution;	36%

Nitroethane (79-24-3) → 3,4,5-trimethylisoxazole (10557-82-1) + 1,1-dinitroethane (600-40-8)

Conditions	Yield
With sodium hydroxide; ammonium persulfate; sodium nitrite In water at 0 - 10℃; for 1h;	A 35% B 15%

1,1-Dinitroethyl-phenyl-sulfid (37771-53-2) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With hydrogenchloride In dichloromethane at 20℃; for 1h; Product distribution;	28%

C2H3KN2O2 → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With sulfuric acid; HO5S(1-)*K(1+); dihydrogen peroxide In water at -10 - 20℃;	11%

piperidine (110-89-4) + diethyl ether (60-29-7) + 1,1-dinitrobromoethane (5432-38-2) → 1,1-dinitroethane (600-40-8)

2-acetylpropanoic acid ethyl ester (609-14-3) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

ethyl isopropyl ketone (565-69-5) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

5-methyl-3-hexanone (623-56-3) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

ethylnitrolic acid → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

ethanol (64-17-5) + 1,1-dinitrobromoethane (5432-38-2) + sodium diethylmalonate (996-82-7) → 1,1-dinitroethane (600-40-8)

ethanol (64-17-5) + 5-methyl-2,2-dinitro-hexan-3-one → 3-methylbutyric acid (503-74-2) + 1,1-dinitroethane (600-40-8)

Conditions	Yield
beim Kochen;

2-pentanol (584-02-1) → 2,3-Pentanedione (600-14-6) + 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

n-hexan-3-one (589-38-8) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

pentan-3-one (96-22-0) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

butanone (78-93-3) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

iso-butanol (78-92-2, 15892-23-6) → 1,1-dinitroethane (600-40-8) + dimethylglyoxal (431-03-8)

Conditions	Yield
With nitric acid

silver dinitromethanide (12281-47-9) + methyl iodide (74-88-4) → 1,1-dinitroethane (600-40-8)

1,1,1-trinitroethane (595-86-8) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With potassium iodide In methanol

3,3-dinitro-butan-2-ol (16454-39-0) → 1,1-dinitroethane (600-40-8) + acetaldehyde (75-07-0)

Conditions	Yield
With water at 25℃; Equilibrium constant; Rate constant;

1-chloro-3,3-dinitro-butan-2-ol (31058-71-6) → 2-chloroethanal (107-20-0) + 1,1-dinitroethane (600-40-8)

Conditions	Yield
With water at 25℃; Equilibrium constant; Rate constant;

Nitroethane (79-24-3) + tetranitromethane (509-14-8) → trinitromethane (517-25-9) + 1,1-dinitroethane (600-40-8)

Conditions	Yield
With hydroxide In ethanol at 25℃; Rate constant; Mechanism; Product distribution; var. pH, aerobic cond., deoxygenated solution, presence of inhibitor;

Nitroethane (79-24-3) → 1,1-dinitroethane (600-40-8) + acetaldehyde (75-07-0)

Conditions	Yield
at 37℃; for 8h; Mechanism; 2-nitropropane oxidase, potassium phosphate buffer (pH 8.0);

1-chloro-1-nitroethane (598-92-5) → 1,1-dinitroethane (600-40-8)

Conditions	Yield
With sodium hydroxide; sodium persulfate; sodium nitrite Rate constant; Kinetics; KOH, K2S2O8, KNO2; presence of 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl.;
With potassium hydroxide; dipotassium peroxodisulfate; sodium nitrite In water at 30℃; Rate constant; Mechanism; various concentration of potassium persulfate;
With sodium nitrite at 30℃; for 0.233333h; Rate constant; Mechanism; influence of superoxidedismutase and hydroquinone on the accumulation of 1,1-dinitroethane; var. time;
With potassium hydroxide; dipotassium peroxodisulfate; sodium nitrite In water at 30℃; Yield given;

1-chloro-1-nitroethane (598-92-5) → 1,1-dinitroethane (600-40-8) + 2,3-Dinitro-2-butene (28103-68-6) + acetaldehyde (75-07-0) + acetic acid (64-19-7)

Conditions	Yield
With dipotassium peroxodisulfate; potassium nitrite In water at 30℃; Product distribution; Rate constant; Mechanism; var. conc., var. pH, with or without presence of dissolved O2, without K2S2O8;

formaldehyd (50-00-0) + 1,1-dinitroethane (600-40-8) + propan-1-ol-3-amine (156-87-6) → 3-(2,2-dinitropropyl)tetrahydro-1,3-oxazine

Conditions	Yield
In water at 20℃; for 2h;	96%

1,1-dinitroethane (600-40-8) + Phenyl vinyl ketone (768-03-6) → 2,2-dinitro-5-phenyl-5-pentanone (36429-12-6)

Conditions	Yield
With ammonium hydroxide In ethanol at 20 - 25℃; for 48h; 1.) 20 deg C, 15 min, 2.) from 65 to 70 deg C, 3 h;	90%
With sodium ethanolate

acrylic acid n-butyl ester (141-32-2) + 1,1-dinitroethane (600-40-8) → butyl 4,4-dinitropentanoate (1429122-80-4)

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 3h;	87%

1,1-dinitroethane (600-40-8) + heptyl acrylate (2499-58-3) → heptyl 4,4-dinitropentanoate (1429122-83-7)

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 3h;	83%

pentyl acrylate (2998-23-4) + 1,1-dinitroethane (600-40-8) → pentyl 4,4-dinitropentanoate (1429122-81-5)

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 3h;	82%

1,1-dinitroethane (600-40-8) + octyl acrylate (2499-59-4) → octyl 4,4-dinitropentanoate (1429122-84-8)

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 4h;	82%

octane-3-yl acrylate + 1,1-dinitroethane (600-40-8) → octane-3-yl 4,4-dinitropentanoate (1429122-85-9)

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 5h;	80%

formaldehyd (50-00-0) + 1,1-dinitroethane (600-40-8) + C14H12N6O2 (634900-36-0) → C17H16N8O6

Conditions	Yield
Stage #1: formaldehyd; C14H12N6O2 In methanol; water at 0 - 5℃; for 0.166667h; Stage #2: 1,1-dinitroethane In methanol; water at 20 - 55℃; for 1.25h;	78%

1,1-dinitroethane (600-40-8) + N-(Carboaethoxy-imino-methyl)-urethan (18804-90-5) → (1-Ethoxycarbonylamino-2,2-dinitro-propyl)-carbamic acid ethyl ester (212264-97-6)

Conditions	Yield
In dichloromethane at 20℃; for 96h;	77%

formaldehyd (50-00-0) + 1,1-dinitroethane (600-40-8) + C2H4N6O2 (634900-34-8) → C5H8N8O6

Conditions	Yield
Stage #1: formaldehyd; C2H4N6O2 In methanol; water at 0 - 5℃; for 0.166667h; Stage #2: 1,1-dinitroethane In methanol; water at 20 - 55℃; for 1.25h;	73%

1,1-dinitroethane (600-40-8) + orthoformic acid triethyl ester (122-51-0) + urethane (51-79-6) → Tris-(aethoxycarbonylamino)-methan (18804-87-0) + (1-Ethoxycarbonylamino-2,2-dinitro-propyl)-carbamic acid ethyl ester (212264-97-6)

Conditions	Yield
In toluene Heating;	A 14% B 72%

1,1-dinitroethane (600-40-8) + 2-(2,2-dinitropropyl)acrylaldehyde (666728-78-5) → 2-(2,2-dinitropropyl)-4,4-dinitropentanal (666728-79-6)

Conditions	Yield
In methanol at 20 - 25℃; for 10h;	70%

1,1-dinitroethane (600-40-8) + acrolein (107-02-8) → 4,4-dinitropentanal (5437-68-3)

Conditions	Yield
With ammonium hydroxide In ethanol at 20℃; for 12h;	66%
With diethyl ether; N-benzyl-trimethylammonium hydroxide

1,1-dinitroethane (600-40-8) + benzamide (55-21-0) + orthoformic acid triethyl ester (122-51-0) → N,N',N''-methanetriyl-tris-benzamide (106404-83-5) + C17H16N4O6

Conditions	Yield
In toluene Heating;	A 55% B 9%

formaldehyd (50-00-0) + 1,1-dinitroethane (600-40-8) + C4H8N6O2 (634900-35-9) → C7H12N8O6

Conditions	Yield
Stage #1: formaldehyd; C4H8N6O2 In methanol; water at 0 - 5℃; for 0.166667h; Stage #2: 1,1-dinitroethane In methanol; water at 20 - 55℃; for 1.25h;	54%

Allyl acetate (591-87-7) + 1,1-dinitroethane (600-40-8) → 4,4-dinitro-pent-1-ene (5432-39-3)

Conditions	Yield
With potassium methanolate; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In isopropyl alcohol at 75℃; for 5h;	50%

3-penten-2-one (625-33-2) + 1,1-dinitroethane (600-40-8) → 3-Methyl-2,2-dinitro-5-hexanone

Conditions	Yield
With ammonia; water In methanol; water at 20℃; for 24h; Condensation;	50%

1,1-dinitroethane (600-40-8) + orthoformic acid triethyl ester (122-51-0) + Propionamid (79-05-0) → 1,1,1-tris(propionamido)methane (94934-58-4) + N-(2,2-Dinitro-1-propionylamino-propyl)-propionamide

Conditions	Yield
In toluene Heating;	A 42% B 12%

acetamide (60-35-5) + 1,1-dinitroethane (600-40-8) + orthoformic acid triethyl ester (122-51-0) → 1,1,1-tris(acetamido)methane (29284-49-9) + 1-Acetylamino-1-ethoxy-2,2-dinitropropane + N-(1-Acetylamino-2,2-dinitro-propyl)-acetamide

Conditions	Yield
In toluene Heating;	A 38% B 15% C 26%

isobutylamide (541-46-8) + 1,1-dinitroethane (600-40-8) + orthoformic acid triethyl ester (122-51-0) → N-[Bis-(3-methyl-butyrylamino)-methyl]-3-methyl-butyramide + 3-Methyl-N-[1-(3-methyl-butyrylamino)-2,2-dinitro-propyl]-butyramide

Conditions	Yield
In toluene Heating;	A 36% B 28%

1,1-dinitroethane (600-40-8) + formamide (77287-34-4, 77287-35-5, 60100-09-6) + orthoformic acid triethyl ester (122-51-0) → tris(formylamino)methane (4774-33-8) + N-(1-Formylamino-2,2-dinitro-propyl)-formamide

Conditions	Yield
In toluene Heating;	A 31% B 8%

1,1-dinitroethane (600-40-8) + 2-(2,2-dinitropropyl)acrylaldehyde (666728-78-5) → 2-(2,2-dinitropropyl)-4,4-dinitropenatanoic acid

Conditions	Yield
Radionov catalyst In diethyl ether at 20℃; for 19h;	31%

Upstream product

• 78-93-3 butanone 
• 10544-72-6 dinitrogen tetraoxide 
• 135636-66-7 butane-2,3-dione mono-oxime 
• 7697-37-2 nitric acid 
• 96-22-0 pentan-3-one 
• 106-35-4 heptan-3-one 
• 7732-18-5 water 
• 110-89-4 piperidine 
• 60-29-7 diethyl ether 
• 5432-38-2 1,1-dinitrobromoethane 
• 79-24-3 Nitroethane 
• 5337-93-9 4'-methylpropiophenone 
• 6921-12-6 4,4-dinitrovaleriansaeure-methylester 
• 565-69-5 ethyl isopropyl ketone 

Downstream Products

• 15473-20-8 5,5-Dinitro-hexanon-(2) 
• 14680-85-4 1-Brom-1,3,3-trinitro-2-phenylbutan 
• 7803-49-8 hydroxylamine 
• 5470-11-1 hydroxylamine hydrochloride 
• 7664-41-7 ammonia 
• 75-07-0 acetaldehyde 
• 64-19-7 acetic acid 
• 10565-52-3 ethanenitrolic acid α,α-dinitroethyl ether 
• 18804-87-0 Tris-(aethoxycarbonylamino)-methan 
• 212264-97-6 (1-Ethoxycarbonylamino-2,2-dinitro-propyl)-carbamic acid ethyl ester 
• 4774-33-8 tris(formylamino)methane 
• 106404-83-5 N,N',N''-methanetriyl-tris-benzamide 
• 5432-39-3 2,2-Dinitro-4-penten 
• 26077-38-3 4,4-Dinitropentanenitrile 

Relevant articles and documents

Bicentral oxidation of nitrosolic acids: Synthesis of 1,1-dinitroalkanes

gem-Dinitrozo compounds are cleanly oxidized into the gem-dinitro analogues on treatment with formic acid/hydrogen peroxide system.

Reaction of nitrosolic acid salts with dinitrogen tetraoxide

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Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions

Electrolysis of salts of primary and secondary nitro compounds (nitroethane, 1- and 2-nitropropanes, nitrocyclohexane, and nitrocycloheptane) in the presence of excess halide, nitrite, cyanide, and phenylsulfinate anions under undivided and divided amperostatic electrolysis conditions in a two-phase medium (CH2Cl2/H2O) produces geminal nitrohalides (35-85% yields), dinitro compounds (15-51%), nitronitriles (6-27%), and nitrosulfones (50-70%). The salts of secondary nitro compounds form the products of oxidative coupling with halide and phenylsulfinate anions under the undivided electrolysis conditions. In all other cases, divided electrolysis is required.